(1R,1'S,3'R,4'aR,5R,6'S,8'aR)-3',4',4'a,5',6',7',8',8'a-octahydro-3'-methoxy-6'-[(p-methoxybenzyl)oxy]-5',5',8'a-trimethyl-5-[2-(trimethylsilyl)ethoxy]-1'-vinylspiro(2-cyclopentene-1,2'(1'H)-naphthalene)-1'-ol

Base Information

• Chemical Name: (1R,1'S,3'R,4'aR,5R,6'S,8'aR)-3',4',4'a,5',6',7',8',8'a-octahydro-3'-methoxy-6'-[(p-methoxybenzyl)oxy]-5',5',8'a-trimethyl-5-[2-(trimethylsilyl)ethoxy]-1'-vinylspiro(2-cyclopentene-1,2'(1'H)-naphthalene)-1'-ol
• CAS No.: 184637-31-8
• Molecular Formula: C₃₃H₅₂O₅Si
• Molecular Weight: 556.858
• Mol file: 184637-31-8.mol

Synonyms:(1R,1'S,3'R,4'aR,5R,6'S,8'aR)-3',4',4'a,5',6',7',8',8'a-octahydro-3'-methoxy-6'-[(p-methoxybenzyl)oxy]-5',5',8'a-trimethyl-5-[2-(trimethylsilyl)ethoxy]-1'-vinylspiro(2-cyclopentene-1,2'(1'H)-naphthalene)-1'-ol

Chemical Property of (1R,1'S,3'R,4'aR,5R,6'S,8'aR)-3',4',4'a,5',6',7',8',8'a-octahydro-3'-methoxy-6'-[(p-methoxybenzyl)oxy]-5',5',8'a-trimethyl-5-[2-(trimethylsilyl)ethoxy]-1'-vinylspiro(2-cyclopentene-1,2'(1'H)-naphthalene)-1'-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,1'S,3'R,4'aR,5R,6'S,8'aR)-3',4',4'a,5',6',7',8',8'a-octahydro-3'-methoxy-6'-[(p-methoxybenzyl)oxy]-5',5',8'a-trimethyl-5-[2-(trimethylsilyl)ethoxy]-1'-vinylspiro(2-cyclopentene-1,2'(1'H)-naphthalene)-1'-ol

There total 4 articles about (1R,1'S,3'R,4'aR,5R,6'S,8'aR)-3',4',4'a,5',6',7',8',8'a-octahydro-3'-methoxy-6'-[(p-methoxybenzyl)oxy]-5',5',8'a-trimethyl-5-[2-(trimethylsilyl)ethoxy]-1'-vinylspiro(2-cyclopentene-1,2'(1'H)-naphthalene)-1'-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

vinyl magnesium bromide (1826-67-1) + (1R,3'R,4'aR,5R,6'S,8'aR)-3',4',4'a,5',6',7',8',8'a-octahydro-3'-methoxy-6'-[(p-methoxybenzyl)oxy]-5',5',8'a-trimethyl-5-[2-(trimethylsilyl)ethoxy]spiro[2-cyclopentene-1,2'(1'H)-naphthalene]-1'-one (184637-36-3) → (1R,1'S,3'R,4'aR,5R,6'S,8'aR)-3',4',4'a,5',6',7',8',8'a-octahydro-3'-methoxy-6'-[(p-methoxybenzyl)oxy]-5',5',8'a-trimethyl-5-[2-(trimethylsilyl)ethoxy]-1'-vinylspiro(2-cyclopentene-1,2'(1'H)-naphthalene)-1'-ol (184637-31-8)

Guidance literature:

In tetrahydrofuran;

DOI:10.1016/S0040-4039(96)02247-2

Reference yield:

C30H46O5Si (184759-78-2) → (1R,1'S,3'R,4'aR,5R,6'S,8'aR)-3',4',4'a,5',6',7',8',8'a-octahydro-3'-methoxy-6'-[(p-methoxybenzyl)oxy]-5',5',8'a-trimethyl-5-[2-(trimethylsilyl)ethoxy]-1'-vinylspiro(2-cyclopentene-1,2'(1'H)-naphthalene)-1'-ol (184637-31-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / Ag₂O, calcium sulfate / 20 h

2: 96 percent / tetrahydrofuran / 12 h / Ambient temperature

With calcium sulfate; silver(l) oxide; In tetrahydrofuran;

DOI:10.1021/ja971527n

Reference yield:

(1S,4'aR,6'S,8'aR)-4'a,5',6',7',8',8'a-hexahydro-6'-[(p-methoxybenzyl)oxy]-5',5',8'a-trimethyl-5-[2-(trimethylsilyl)ethoxy]spiro[2-cyclopentene-1,2'(1'H)-naphthalene]-1',3'(4'H)-dione → (1R,1'S,3'R,4'aR,5R,6'S,8'aR)-3',4',4'a,5',6',7',8',8'a-octahydro-3'-methoxy-6'-[(p-methoxybenzyl)oxy]-5',5',8'a-trimethyl-5-[2-(trimethylsilyl)ethoxy]-1'-vinylspiro(2-cyclopentene-1,2'(1'H)-naphthalene)-1'-ol (184637-31-8)

Guidance literature:

Multi-step reaction with 3 steps

1: (i-Bu)2AlH / hexane; tetrahydrofuran / 1.5 h / -10 °C

2: 96 percent / Ag₂O, calcium sulfate / 20 h

3: 96 percent / tetrahydrofuran / 12 h / Ambient temperature

With calcium sulfate; diisobutylaluminium hydride; silver(l) oxide; In tetrahydrofuran; hexane;

DOI:10.1021/ja971527n

upstream raw materials:

vinyl magnesium bromide

(1R,3'R,4'aR,5R,6'S,8'aR)-3',4',4'a,5',6',7',8',8'a-octahydro-3'-methoxy-6'-[(p-methoxybenzyl)oxy]-5',5',8'a-trimethyl-5-[2-(trimethylsilyl)ethoxy]spiro[2-cyclopentene-1,2'(1'H)-naphthalene]-1'-one

C₃₀H₄₆O₅Si

C₃₀H₄₆O₅Si

Downstream raw materials:

(Z)-(2R,4R,6S,9R,13S,15R)-2,10-Dimethoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-tricyclo[11.2.1.0^4,9]hexadeca-1⁽¹⁶⁾,10-dien-15-ol

[(Z)-(2R,4R,6S,9R,13R)-2,10-Dimethoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-tricyclo[11.2.1.0^4,9]hexadeca-1⁽¹⁶⁾,10,14-trien-15-yloxy]-trimethyl-silane

(Z)-(2R,4R,6S,9R,13R)-14-Dimethylaminomethyl-2,10-dimethoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-tricyclo[11.2.1.0^4,9]hexadeca-1⁽¹⁶⁾,10-dien-15-one

(Z)-(2R,4R,6S,9R,13R)-2,10-Dimethoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-14-methylene-tricyclo[11.2.1.0^4,9]hexadeca-1⁽¹⁶⁾,10-dien-15-one